Sodium Iodide → 8-bromo-1-[(diethylamino)methyl]-6-(2-pyridyl)-4H-s-triazolo [4,3-a][1,4]benzodiazepine

HRID 1731130Notes

Reaction equation

HRID 1731130 reaction equation
[CH2:1]([NH:3][CH2:4][CH3:5])[CH3:2].[Br:6][C:7]1[CH:8]=[CH:9][C:10]2[N:16]3[C:17]([CH2:20]Cl)=[N:18][N:19]=[C:15]3[CH2:14][N:13]=[C:12]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][N:23]=3)[C:11]=2[CH:28]=1.[I-].[Na+]>CN(C)C=O>[Br:6][C:7]1[CH:8]=[CH:9][C:10]2[N:16]3[C:17]([CH2:20][N:3]([CH2:4][CH3:5])[CH2:1][CH3:2])=[N:18][N:19]=[C:15]3[CH2:14][N:13]=[C:12]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][N:23]=3)[C:11]=2[CH:28]=1

Participants

5

Reactant 3

HCID 5238Sodium IodideHCID 8021DiethylamineHCID 203612008-bromo-1-(chloromethyl)-6-(2-pyridyl)-4H-s triazolo[4,3-a][1,4]benzodiazepine

Product 1

HCID 203612248-bromo-1-[(diethylamino)methyl]-6-(2-pyridyl)-4H-s-triazolo [4,3-a][1,4]benzodiazepine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 1 ml. of diethylamine in 5 ml. of dry dimethylformamide, 350 mg. of 8-bromo-1-(chloromethyl)-6-(2-pyridyl)-4H-s-triazolo[4,3-a][1,4]benzodiazepine (obtained as in Preparation 3) is added and the mixture stirred under nitrogen at room temperature for about 4.5 hours. To the mixture, 50 mg. of sodium iodide is added and stirring is continued at room temperature for about 18 hours and then heated at about 100 to about 110° C. for about an additional 6 hours. It is then poured into ice water and extracted with chloroform. The extract is washed with water, dried over anhydrous potasssium carbonate and concentrated under vacuum. The residue is crystallized from ethyl acetate: Skellysolve B to give pure 8-bromo-1-[(diethylamino)methyl]-6-(2-pyridyl)-4H-s-triazolo[4,3-a][1,4]benzodiazepine (I).

Workup

  1. stirringstirring
  2. waitis continued at room temperature for about 18 hours
  3. temperatureheated at about 100 to about 110° C. for about an additional 6 hours
  4. extractionextracted with chloroform
  5. washThe extract is washed with water
  6. dry with materialdried over anhydrous potasssium carbonate
  7. concentrationconcentrated under vacuum
  8. customThe residue is crystallized from ethyl acetate

Sources & evidence

ORD record
ord-855eb0fe384e49ac9b3e272bd4dfe42b
Source dataset
uspto-grants-1976_11
Patent number
US03995043

Reaction notes

Loading…